Old Boss Stories

188,080 results
Orientation
Length
Source
Infinite Scroll

Wimp Loses to Young Black Boss Ch. 02

by michaelwimphusband on Sep 19, 2017
Interracial Love

Chapter Two of a true story Following the humiliating events of his college days Myron went to work for a small, executive firm in Marketing and Development. There, he honed his skills and climbed the corporate ladder very well over the next 12 and a half years. He saved nearly every dime he could in the hopes of providing for his future and future wife. Ho...

Winchester's Intern to Slut Program

by AruziaMelnik on Nov 4, 2019
Erotic Couplings

Author's Note: I worked on this story on and off for about 2 years. As readers of my previous story know, I need to take frequent breaks because writing these stories for you is so arousing. This one was no different. I hope you enjoy reading it as much as I did writing it. * Jade ran into Mr. Winchester's office, out of breath, her ample cleavage rising a...

Marty's Submission Ch. 01

by PuppyLov3r on Aug 18, 2017
Fetish

Marty. Marty Peg. She was unknowingly selected, not for testing or for observation, not to see what tv shows are the best or worst, not to see how she changed from child to women. No. Marty was selected to see what influences make teens more suicidal and which make them less. So in some way it is observation and testing, though more general observation...

An All Family Business

by MitchFraell on Sep 17, 2017
Loving Wives

This is a fantasy. Any similarity between this story and any actual incidents are pure coincidental. I had always regarded my mother-in-law as a remarkable woman. When I first met her, Barbara was approaching 50 years of age. She was, and still is for that matter, a vivacious, attractive and intelligent lady. She had held down a busy and demanding job for...

Under New Management

by DontJudgeMe on Sep 26, 2017
Erotic Couplings

The two men stepped into the Happy Gent, and immediately their senses were assaulted by the strange, exotic place. The beat of the dance-music was almost tangible, though the music was not overly loud. Their eyes were forced to adjust to the shady corners where little light shone as well as the lit stage. But the most noticeable difference from the outside w...

Manipulating Jenny Ch. 04

by BeamMeUp on Sep 18, 2017
Exhibitionist & Voyeur

Summary: Voluptuous 18 year-old office flirt Jenny in stockings and garter belt, helps her boss make a decision, and she learns of another woman wanting to meet her for a lesbian encounter. Tuesday arrives a week after Jenny's 55 year-old grey haired boss says he will discuss giving her a substantial pay rise. He gives her the day off so the staff will not...

Goldie Pt. 02: The Man with a Golden Penis

by erectus123 on Nov 8, 2017
Erotic Couplings

GOLDIES' JOB AT JOY GARDEN MASSAGE PALACE As you know from Part One, I am serving a death sentence here in the Texas Penitentiary for a murder I did not commit. The man I am charged with murdering was like a father to me and his wife was way more than motherly to me, why would I wish good Christian folk like them no good? Well, there is no reason, I swear,...

Sex with The Boss

by knightangel on Sep 17, 2017
Mature

Keith Miles, age 23 single jet black hair, and very successful in his job for the past 7 months in marketing. His past jobs never got him very far, thanks to his mother's friend Jane, it got him the best job in the city of Dallas. Miss Jane Henson, age 48 but looks like she's 34 has long blonde hair, and a full figured hourglass body with a 32D chest. She ha...

File Under T

by SinisterSpiders on Sep 13, 2017
Erotic Couplings

Christina smiled happily as she looked at the time on the start bar of her monitor. Quarter past five in the afternoon and everything was up to date. She had done the filing, made all the necessary travel arrangements for her boss and even managed to get some letters typed up that didn't need to be sent until Friday. Third day on the job and Christina had it...

Giving Him My Anus Ch. 02

by naughtysexmouse on Sep 18, 2017
Anal

For more than a week after Mr Taylor had taken my anal virginity in a hotel room, I did not see or hear from him at all. I had replayed the sordid encounter in my head countless times, and often felt my pussy clench involuntarily when I pictured the scene as it had unfolded. Even after the tenderness in my arse had faded I couldn't stop thinking about the mi...